Running A Startup Is Hard,­ Really Hard

Running A Startup Is Hard,­ Really Hard

Running A Startup Is Hard,­ Really Hard

I’ve been running a startup for over a year now and the emotional rollercoaster that comes with it makes you wonder why anyone signs up for this.

As if entrepreneurialism wasn’t difficult enough, being an entrepreneur and running a high-risk startup is just adding fuel to the fire. But through it all, I’ve learned a few techniques that help you stay sane. Understand That Today Is (Most Likely) The Worst Day. In most cases, startups get better/easier over time.

That’s not to say that they will ever be “easy”, but a year ago today we were nothing.

  • We had no customers.
  • We had an awful product.
  • We had a small team.

We’re far from successful, but on almost any metric that you would use to indicate the success of a business, we’re better off today than we were a year ago.

achieve goals

We have customers, a few hundred in fact. The product is pretty good, though it has to be better. We have a bigger team and have taken on help where it counts. And we’ve learned so much about what to do and especially what NOT to do. And every day I know that we’re getting a little bit better. We’re realizing things we didn’t know before. We’re adding new features. We’re acquiring new customers.

team work

It may not be exactly day for day (in fact it never is), but month to month, but we’re improving, and that’s what helps us survive the day to day ups and downs. Measure Progress In Months. Let’s continue with that whole day to day thing.

I’ve had the following happen more times than I can imagine:

  • A week that started off slow, that ended on a high note with a lot of sign ups.
  • A week without much progress, that ended with the release of a big, new feature.
  • A week that started with a fight between founders, which ended with us more aligned than ever before.

The fact is, there are bad days. There are days that make me think the business is completely imploding and question why I started it in the first place.


But when I look back at each month, it’s always better than the last.

So what I’ve done is stopped measuring things in days. I stopped obsessing about the analytics every day (though I still do look at them out of habit). I stopped psyching myself that previous successes were just flukes.

I look for progress at a pace that fits our business.


And in doing so I feel less stressed. Take Breaks And Don’t Feel Guilty. I’ve been known to put in 60 and 70 hour weeks. In fact, it’s not even that hard. Most days I check my time tracking dashboard and I’m amazed at how “quickly” 11 hours flew by. To some extent, that’s a good thing. I remember being at work, doing the traditional 9 to 5, and wondering how the heck was I going to get through the day.

And that was barely a 40 hour week. The startup takes control of you and you burn, and burn, and burn. But it’s important not the burnout, and that’s where breaks come in. I take breaks whenever I need to. Sometimes it’s a weekend. Sometimes it’s a weekday. Sometimes it’s in the morning, afternoon, or night.


But the thing that you have to do is to not feel guilty about it. In fact, today was largely a break. I wrote this article, and did a few other things, but overall I didn’t get too much done. It’s Sunday, and I worked a long week, and I’m going to take it easy, and not feel guilty.

Enjoy What I Do

When it comes down to it you have to enjoy what you do.

Now, I don’t enjoy every little part of my day or every project I work on - but as a whole, yes, I like running a software business. I like learning about software, experimenting with different marketing strategies, working with motivated, hard-working people, and building a product that people are using to derive real value from. 

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If I didn’t enjoy what I did I don’t know how I could show up every day and work 8, 9, 10 hours. It’s hard to create this after the fact - you have to plan ahead. You can do that by thinking about the business model, the customer you’ll have, and what the day to day requirements will be. After all, if you don’t enjoy what you’re doing - what’s the point?